How to Have a Productive Workation With Your Team (We’ve done it, and so can you!)

About Kari DePhillips

Kari DePhillips is the owner of The Content Factory and co-founder of Workationing. She's been featured everywhere from Fast Company to Forbes to NBC News for her management style and digital marketing expertise, and Thrive calls her a "limit‑breaking female founder." See all posts by Kari DePhillips.

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This photo taken while working from the beach in Mexico. More inspiring to look at than three walls of a cubicle, right?

By now you’ve probably heard of Noelle Hancock, the 31-year-old journalist who quit her job to scoop ice cream in the Caribbean. It’s no huge surprise that her story went viral – who doesn’t dream about trading in their responsibilities for a beach cabana and an unending supply of piña coladas?

Once you realize that your employees are having that fantasy, though, you can help them turn it into a reality – plus get some extra work, calm and creativity out of them in the process. It’s called a “workation” (working vacation), and we’re big fans at TCF.

A yearly, or even quarterly, workation can be a total game changer for your business (or at the very least, your perspective), and it’s something that The Content Factory has fully embraced. The Internet, combined with companies like Airbnb and Uber, make working outside of the office easier and more affordable than ever before in human history.

Since we can all work from anywhere, why don’t we? This is a question we asked ourselves last year, and the answer took us all the way to Puerto Rico for a couple of weeks on TCF’s first workation. And Hawaii, then, California. And after that we went to D.C. and New York City.

If you can work from home, you can work from the Caribbean (in fact, we’re on a team workation in Mexico as we write this blog post). The best part of taking a workation is that when you and your employees go back home and have a Saturday/Sunday to recoup, you’re all totally refreshed and ready to dip back into the old routine, which suddenly doesn’t seem nearly as monotonous as it was before.

This may help sell you on packing up your office to go work with some sand between your toes, but how do you make sure you all stay productive when you’re in a new and exotic location? Below is a list of tips that have consistently worked for us – follow these steps, and you may even be more productive on the beach than you were at the office.

Choosing the Right Location for Your Workation

Where to wander? If you ask us, the best place for a workation is the beach — it’s the perfect locale to relax and unwind, which is exactly what you’ll want to do after spending the morning working on a report. However, not everyone loves rocking a string bikini, so before you book flights to Cancun, talk to your team and ask them where they feel the most relaxed. You may all agree on a charming cottage in the French countryside or a cabin in the Rockies. Remember, you want your employees to have a great time, not force them to pretend like they are while you go on your own personal adventure.

Book with Airbnb. From a purely financial standpoint, you can’t do much better than the prices on Airbnb, but what makes these homes and apartments the best choice for your workation is the amount of space they provide. You can get an entire 5-bedroom house for significantly less than the cost of five hotel rooms, plus you’ll have your own kitchen (and, if you book the right place, a hot tub and swimming pool). Airbnb makes it easy for you to make the right choice for lodging, because there’s extensive info and reviews on each location. Make sure to check for these things before you book:

Wifi (and reviews that mention it’s working and up-to-speed)

A full kitchen (so you won’t need to eat out for every meal)

A location that’s central to restaurants, grocery stores and attractions

A high rating, not just for the location but for the host

Lots of space, including things like balconies, patios and pool areas — switching up which space you work in will keep you from zoning out

To make sure your solitude won’t be obliterated by spring breakers doing body shots, email your Airbnb host to see make sure your location isn’t surrounded by nightclubs. Also ask if any construction is being done on the building — because nothing thwarts a conference call like the sound of a jackhammer.

Photo of the hot tub and pool at the hacienda-style Airbnb we rented for TCF’s recent workation

Make Sure You’re Fully Prepared for Your Workation

1. Pick your workationing team.

Your workation will work best if you spend it with the right members of your company. Invite only employees who won’t bring drama with them and make sure you don’t create any of your own by passing up veteran employees while offering spots to new recruits. At TCF, workations are earned — and you have to be with the team for at least a year before you’re invited along. Although you may be tempted to allow +1s to join the party, remember that this is a workation, not a group vacation. If you want to maximize productivity, you’ll need to limit this trip to employees only.

2. Set expectations.

Create two to-do lists for each employee — one for tasks they need to complete before leaving and one that includes their responsibilities and daily goals while away. This way, employees will always have something to do and won’t have to interrupt anyone to ask, “what now?”

3. Work ahead.

Make sure things like social media posts are scheduled for your day of travel and even the day after — you never know what might happen! We’ve had team members end up with canceled and/or delayed flights, which put them in the workation destination 24+ hours past when they were supposed to get there. If there are projects due while you’ll be away, see how many you can knock out ahead of time so you won’t have to scramble and stress.

4. Pack to win.

You don’t need a bunch of crazy productivity hacks to make your team work efficiently while they’re on a workation, but you do need to pack smart and that means you’ll need these things:

A back-up hotspot (you can likely tether your phone, but figure this out before you leave so you aren’t on the phone with Verizon from Peru).

Every portable charger you own.

Outlet converters if travelling overseas.

At least one additional device (a tablet’s a good choice) in case someone has laptop issues.

Sort out cell phones and banking.

If you’re traveling outside the US, you’ll need to change your data plan for that period. You’ll also need to notify the banks for any cards you plan to use a week in advance so they don’t freeze your accounts for suspicious activity. Make sure everyone has this figured out before you leave, so you don’t waste valuable work time later.

Productivity Bonus: Consider Knocking Out a Big Team Project

Group workations can be a great team building exercise — they’re even better than the trust falls you did at summer camp as a kid. One way to help solidify the team-building aspect of your workation is to knock out a big group project together. For us, on this trip, it’s reworking TCF’s website copy and developing a series of webinars.

When you rally the troops behind a common cause (and make it clear that the battle is going to be won before the workation’s over), you’ll find that everyone comes together to get the job done. This is a sneaky way to get more out of your employees while giving them a little something extra in return.

4 Ways to Increase Productivity During Your Workation

1. Start by stocking the fridge.

Your first impulse upon touching down in Jamaica will probably be to throw on your swimsuit and head to the beach. Try to hold off at least long enough to make a grocery run. Get food for simple breakfasts and lunches, along with staples like coffee and other drinks. When you’re on vacation, a simple coffee run can lead to hours of exploring, and a well-stocked kitchen can keep you inside and on-task.

2. Schedule late afternoon excursions.

The best times to work on your workation will be early in the morning and before bed. As Parkinson’s Law states, “work expands so as to fill the time available for its completion” so scheduling a trek of Mayan ruins for 4pm is a great way to get everyone motivated to knock tasks off their to-do lists quickly.

3. Track your time.

Shaking up your routine is a good thing, but it will make it harder to gauge exactly how much time you’re putting in each day — and if each member of your team is pulling their weight. Have everyone track their time using Toggl and check their progress throughout your stay.

4. Be a grownup.

This is not the time to relive your college years by getting totally wasted every night until dawn, and your employees should get the memo. Keep reasonable sleeping and waking hours (pro tip: make breakfast for everyone at 8 or 8:30 to set the rise-and-shine schedule early). With that said, make sure to set one or two days (the weekend is probably best) for people to cut loose a little — without having to work the next day. Once everyone frees their inner party animal, they’ll be ready to buckle down and get to work on Monday.

Remember: Workations Only Work If You Do

Although each of these tips can help you increase productivity on your workation, the best way to remain productive while you travel is to keep this in mind — if you kick ass on one workation, you can take another (and another, and another). Not everyone has the ability to end their workday with a trek through a forest of redwoods or a dip in the Caribbean, so if you’re one of the lucky few who can, you owe it to yourself to make the most of it.

Need specific advice on planning your next workation?

The Content Factory team has gotten their workation on everywhere from to Puerto Rico to Australia — drop us a comment and we’ll be happy to answer your questions! And be sure to check out our Workationing podcast, where you can learn tips for having a productive workation while listening to us recount our adventures (and misadventures) in traveling the world while working hard!

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